p-Xylyl bromide → Methyl 2,2-diphenyl-6-(4-methyl-benzyl)-1,3-benzodioxole-4-carboxylate

HRID 2251602Notes

Reaction equation

HRID 2251602 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:23]([O:25][CH3:26])=[O:24])[C:5]2[O:9][C:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[O:7][C:6]=2[CH:22]=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.CC([O-])=O.[K+].Br[CH2:51][C:52]1[CH:57]=[CH:56][C:55]([CH3:58])=[CH:54][CH:53]=1.C([O-])([O-])=O.[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:16]1([C:8]2([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[O:7][C:6]3[CH:22]=[C:2]([CH2:51][C:52]4[CH:57]=[CH:56][C:55]([CH3:58])=[CH:54][CH:53]=4)[CH:3]=[C:4]([C:23]([O:25][CH3:26])=[O:24])[C:5]=3[O:9]2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

7

Reactant 5

HCID 7721p-Xylyl bromideHCID 11430Potassium CarbonateHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 59642990Methyl 6-bromo-2,2-diphenyl-1,3-benzodioxole-4-carboxylate

Product 1

HCID 59643018Methyl 2,2-diphenyl-6-(4-methyl-benzyl)-1,3-benzodioxole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst2×

Procedure

Methyl 6-bromo-2,2-diphenyl-1,3-benzodioxole-4-carboxylate (200 mg, 1.486 mmol, 1 eq.), Pd(PPh3)4 (57 mg, 0.049 mmol, 0.1 eq.), bis(pinacolato)diboron (160 mg, 0.632 mmol, 1.3 eq.) and KOAc (72 mg, 0.73 mmol, 1.5 eq.), then Pd(PPh3)4 (57 mg, 0.049 mmol, 0.1 eq.), 1-bromomethyl-4-methyl-benzene (117 mg, 0.63 mmol, 1.3 eq.) and K2CO3 (336 mg, 2.43 mmol, 5 eq.) were reacted according to GP6 to yield the title product as a colorless, very slowly solidifying oil.

Sources & evidence

ORD record
ord-55be26d1d65448ae942d3cb153ce6268
Source dataset
uspto-grants-2008_01
Patent number
US07319101B2

Reaction notes

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